Jaune's Awakening
by RWBYChar
Summary: When Jaune owes Pyrrha a favor she decides that it's the perfect chance to make him into the boy she wants to be with. Jaune get's a close up view of an "Eiffel Tower" and experiences a Silent Night.
1. Chapter 1 - A Trip to Paris

Jaune's Awakening - RWBY /co/Medy

Written By Char

Chapter One - A Trip to Paris

A few minutes before curfew at Beacon Academy Pyrrha, a member of team JNPR, quickly moved down the hall. Upon reaching the door of team RWBY she looked around to make sure no one was watching. Once she was sure that it was clear she carefully knocked on the door. It opened hastily, the person on the other side expecting this visit.

"Do you have it ready?" Pyrrha whispered.

"Of course." The figure on the other side replied. "Just make sure you don't stretch it too much or Weiss might figure it out." They said, handing Pyrrha a folded up white dress.

"Thanks again." Pyrrha replied as she turned back to return to her room.

"Don't mention it, the thought of what you're doing is worth the trouble."

Once she reached her dorm room Pyrrha silently opened up the door. Creeping in she looked at all of the beds. Jaune was already asleep and Ren and Nora were no where to be found.

"Jaune, wake up" she said as she began to shake her teammate.

"Uh, Pyrrha. Why did you wake me up? I was having this perfect dream about Weiss and..."

"Remember how you said you owed me one for all of the extra training I gave you?" She asked, laying down on top of Jaune.

"Well yeah but... I didn't expect this"

"No buts Jaune. Here, put this on." Pyrrha said as she hopped off of him and revealed the dress she was hiding behind her back.

"Wh-what?"

"Come on Jaune, I'm just going to take a few pictures. It's no big deal."

"I can't wear this! This is Weiss' dress!"

"If you want me to keep training you then you have to, it will only be for a minute. Come on."

"O-okay, but just for a little bit."

Jaune began to strip down to his underwear, clearly uncomfortable that Pyrrha was watching. When he was wearing nothing but his boxers he began to try and fit into Weiss' dress.

"What are you doing?" Pyrrha asked.

"What do you mean?"

"You can't wear those with a dress like this, take off your boxers too." Jaune hesitated but eventually complied with her demand. Once he was wearing the dress Pyrrha began to giggle.

"I-it's not that funn-" But Jaune didn't get a chance to finish his sentence. Pyrrha leaned into him and began to kiss his lips.

Jaune, obviously embarrased about the situation, pushed Pyrrha away.

"W-what are you doing?"

"Let's just have a little fun." Pyrrha replied, giving Jaune a look of desire. Once again Jaune gave in and moved closer to Pyrrha to start kissing her again. After a few seconds Pyrrha turned him around and pushed him towards her bed, eventually throwing him on to it. As Jaune began to ask what was going on Pyrrha reached into her bedside table and pulled out what appeared to be a large black strap on.

"Uh, Pyrrha. What do you plan to do with that" He asked, with a panicked expression on his face.

"It's called Pegging, Jaune. Don't worry, you'll love it."

Pyrrha pulled down her own skirt and panties revealing her soft pussy. Jaune starred in disbelief as she slipped on the strap on she was holding.

"Because it's your first time I'll go easy on you, okay?"

After what felt like hours of Pyrrha slowly working her way in and out of Jaune the other two members of JNPR returned to the dorm room, but Pyrrha and Jaune had yet to finish their "lovemaking".

"Hey guys." Pyrrha said, turning her head away from her lover. "Could you give me a hand over here Nora?"

"Of course! Let's break his ass!" Nora shouted as she sped over to Pyrrha's bedside table and pulled out and equipped herself with a second strap on.

"I don't think asses break, Nora." Ren chimed in.

"That's true, but you can always rip it!" Nora replied while taking her position at Jaune's head. "Now they won't hear you scream!" She exclaimed, entering his mouth.

Despite Jaune's mouth being filled, the three friends did manage to make quite a bit of noise as the two girls rhythmically thrusted into him. After a few minutes a very annoyed Ruby came to the door of team JNPR and after knocking several times without answer she went inside. Peering in she was met with the image of Pyrrha and Nora fucking Jaune in both his holes while they joined hands above him.

"Uhhhh, you look really pretty Jaune." Was all the girl could say as she awkwardly watched her friends. The only response was the sound of a muffled "Thank you" coming from Jaune's mouth as he was filled with Nora's strap on.

"I really need to find some new friends." Ruby mumbled as she quickly left the room to escape from what she just saw.

After making it back to her own room her teammates asked her if she found the source of what was keeping them up all night.

"Well... I found it yeah, but I don't think it's going to stop any time soon. But on the plus side I found your dress Weiss."


	2. Chapter 2 - Silent Night

Jaune's Awakening - RWBY /co/Medy

Written By Char

Chapter Two - Silent Night

It was another long day at Beacon Academy for Jaune Arc. His team had kept him up all night for the last week "sightseeing" and it didn't look like it would end anytime soon. However, despite Jaune's reluctance, things were only getting worse.

"Pyrrha, I can't wear this to class!" Jaune shouted at his team mate.

"Oh come on Jaune, it's just a uniform." She replied.

"A girl's uniform!"

"You didn't seem to have any problems wearing it last night." Jaune's face started to turn red and he looked down at the ground. "The only problem is what we're going to do about your hair... I suppose we'll have to wait until we can give you the full treatment."

"T-the full treatment?"

"Oh come on Jaune, you don't think this is the first time I've done this do you?"

After Jaune changed into his normal uniform he and Pyrrha went downstairs to meet up with team RWBY and the rest of team JNPR.

"So how was last night Pyrrha?" Blake asked, holding back a giggle. "I could hear it perfectly with these." She motioned to her bow.

"Well you know how it is." Pyrrha replied.

"C-could you guys please stop talking about it." Jaune stammered.

"Oh come on Jaune, you don't have to be such a tight-ass." Chimed in Yang. Jaune slumped his head down and quickly left the building, heading towards class.

"I don't think that was appropriate, Yang." Weiss said.

"Oh come on, he's practically asking for it at this point."

...

That afternoon Jaune returned to his dorm to a big surprise. Both Pyrrha and Weiss were standing in the middle of the room preparing multiple bags of supplies. After noticing that he entered the room Pyrrha turned to him and ushered him into a chair.

"I'm sorry Jaune, at first you might not like it but you'll get used to it after a while."

"W-what do you mean Pyrrha?"

"Just sit down and shut up." Weiss said. "After all of this you'll finally be out of my hair."

The two girls stripped him down and although Jaune was uncomfortable he was used to Pyrrha doing this to him. They moved back and forth using dust to create different effects on his hair and body. When they were finally done working on his features they pulled him up and out of the chair and threw different girl's clothes at him. First they made him put on a pair of panties and a bra, although he didn't understand why he needed one. Once those were on they forced him into a brand new dress, one that Weiss bought just for this occasion. After they felt he was ready they guided him over to the mirror that was hanging on the wall in their room.

"What do you think?" Pyrrha asked.

Jaune was completely stunned, they had made him look like a girl! His hair was a lot longer, they had attached extensions using dust to make it look completely natural. If it had been a little bit longer and thicker it would have looked identical to Yang's. His face and body still looked almost the same, but due to make up and the design of the dress he looked simply looked like a muscular women, very much like Pyrrha.

"You look perfect." Pyrrha said to him. Jaune was still shocked, starring into the mirror he couldn't believe his eyes.

"Come on, I know how to cheer you up." Pyrrha dragged him over to the bed and signaled Weiss to join them.

"No! Not now." Jaune pulled away. "I'm going out." He stormed out of the dorm room and slammed the door on his way out.

Yang, after hearing the commotion and walked over to team JNPR's room, burst into laughter.

"Is it his time of the month already?"

Pyrrha quickly ran after Jaune, but lost track of him. She wandered around the campus for a few hours until she eventually found him sitting on a bench alone in the park.

"I'm sorry, Jaune." She said, sitting down next to him. "I thought you would have liked it."

"Well I don't. I just need to be alone right now, okay?" Pyrrha sighed and obliged. She got up and started walking back to the dorms.

"Hey Pyrrha." A voice behind her said.

"Huh?" She responded. "Oh, Cardin. If you excuse me I'm not in the mood right now to have to deal with you."

"Relax. I was just wondering who your friend back there was."

"My friend? You mean Jau-"

"Jau?"

"Oh, I mean... Joan."

"Joan? Well she's pretty cute." A smile crossed Pyrrha's lips.

"I know we don't usually get along, but I'm sure she'd like you Cardin."

"Why's that?"

"Well.. She likes "up-front" guys like you."

"Up-front huh?"

"Yeah, now you two have fun." Pyrrha quickly walked away. She know that Jaune wouldn't be happy right now, but in the long run he would thank her.

The one word that could describe what Jaune was feeling was scared. Cardin was quickly approaching him and he had no idea what Pyrrha had just said to him. He quickly rose and started to walk away from him but he couldn't get very far in the dress they put him in.

"Hey, where you going?" Cardin caught up to him rather easily. "I'm Cardin." Jaune kept his mouth shut, he was unarmed and he knew his voice would give him away.

"Playing hard to get eh?" Cardin got in front of him and tripped him to the ground. "Oops, here let me give you a hand." He grabbed onto the back of Jaune's head and undid his pants. His cock was soon rock hard and he pushed it into Jaune's mouth.

Jaune fought back at first, too afraid to say anything. The harder he fought though the more Cardin got into it. Eventually he realized there was no use fighting and that it was all over. He couldn't believe what he was doing, to get through it he just pretended that it was Nora and that it was just any other night in the JNPR dorm room. Although he didn't enjoy it this made it at least bearable for him. In his head it was nothing that he wasn't used to. Well, that was until Cardin finished.


End file.
